1-Bromo-5-isocyanatopentane → 1-(5-Bromopent-1-yl)-5-(3,4-difluorobenzyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone

HRID 1003745Notes

Reaction equation

HRID 1003745 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH2:16])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]=[C:25]=[O:26]>O>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]1[C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=2)=[C:4]([C:3]([O:2][CH3:1])=[O:17])[NH:16][C:25]1=[O:26]

Participants

4

Reactant 2

HCID 144828831-Bromo-5-isocyanatopentaneHCID 54052828HCID 54052828, compound

Product 1

HCID 187982741-(5-Bromopent-1-yl)-5-(3,4-difluorobenzyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazoloneYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-amino-4-(3,4-difluorophenyl)-3-oxobutyric acid methyl ester (0.100 g, 0.344 mmol) in 2 mL water was added 1-bromo-5-isocyanatopentane (0.3 mL), and the reaction mixture refluxed for 3 hours. The reaction mixture was concentrated and partitioned between EtOAc (30 mL) and 1N HCl (10 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over sodium sulfate, filtered and concentrated to give 0.080 g (55%) of the product as a syrup; 1H-NMR (CDCl3) δ1.36-1.81 (m, 6 H), 3.34 (t, J=6.6 Hz, 2 H), 3.32-3.37 (m, 2 H), 3.86 (s, 3 H), 4.21 (s, 2 H), 6.91-7.16 (m, 3 H), 9.53 (s, 1 H).

Workup

  1. temperaturethe reaction mixture refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc (30 mL) and 1N HCl (10 mL)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8496500ae94c465e81fb73771363abff
Source dataset
uspto-grants-2000_04
Patent number
US06046331

Reaction notes

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